Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer

Carla Rizzo, Francesca D'Anna, Fabiana Pandolfi, Daniele Rocco, Isabella Chiarotto, Leonardo Mattiello, Marta Feroci

Risultato della ricerca: Article

1 Citazione (Scopus)

Abstract

The cathodic reduction of dicationic imidazolium bromides,whose spacer is either an aliphatic chain or a xylyl group, leadsto the formation of the corresponding N-heterocyclic carbenes(NHCs), which were isolated as the corresponding thiones, afterreaction with elemental sulfur. The behaviour of the dicationswas compared with the corresponding monocations. Thebehaviour of dicarbenes depends on the nature of the spacer.This study evidenced that dicarbenes deriving from xylyldications are less stable than the corresponding aliphatic ones(giving lower yields in thiones), due to a debenzylation reaction.On the other hand, the yields in thiones starting from aliphaticdications are higher than the corresponding monocations,suggesting a cooperative reduction at the electrode of the twoimidazolium moieties. The cathodic process was confirmedusing the co-electrogenerated hydrogen to reduce 2,2,2-trifluoroacetophenone to the corresponding alcohol.
Lingua originaleEnglish
pagine (da-a)4275-4283
Numero di pagine9
RivistaChemElectroChem
Volume6
Stato di pubblicazionePublished - 2019

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Thiones
Bromides
Alcohols
Sulfur
Hydrogen
Electrodes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electrochemistry

Cita questo

Rizzo, C., D'Anna, F., Pandolfi, F., Rocco, D., Chiarotto, I., Mattiello, L., & Feroci, M. (2019). Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer. ChemElectroChem, 6, 4275-4283.

Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer. / Rizzo, Carla; D'Anna, Francesca; Pandolfi, Fabiana; Rocco, Daniele; Chiarotto, Isabella; Mattiello, Leonardo; Feroci, Marta.

In: ChemElectroChem, Vol. 6, 2019, pag. 4275-4283.

Risultato della ricerca: Article

Rizzo, C, D'Anna, F, Pandolfi, F, Rocco, D, Chiarotto, I, Mattiello, L & Feroci, M 2019, 'Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer', ChemElectroChem, vol. 6, pagg. 4275-4283.
Rizzo C, D'Anna F, Pandolfi F, Rocco D, Chiarotto I, Mattiello L e altri. Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer. ChemElectroChem. 2019;6:4275-4283.
Rizzo, Carla ; D'Anna, Francesca ; Pandolfi, Fabiana ; Rocco, Daniele ; Chiarotto, Isabella ; Mattiello, Leonardo ; Feroci, Marta. / Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer. In: ChemElectroChem. 2019 ; Vol. 6. pagg. 4275-4283.
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AU - Rizzo, Carla

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AU - Rocco, Daniele

AU - Chiarotto, Isabella

AU - Mattiello, Leonardo

AU - Feroci, Marta

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N2 - The cathodic reduction of dicationic imidazolium bromides,whose spacer is either an aliphatic chain or a xylyl group, leadsto the formation of the corresponding N-heterocyclic carbenes(NHCs), which were isolated as the corresponding thiones, afterreaction with elemental sulfur. The behaviour of the dicationswas compared with the corresponding monocations. Thebehaviour of dicarbenes depends on the nature of the spacer.This study evidenced that dicarbenes deriving from xylyldications are less stable than the corresponding aliphatic ones(giving lower yields in thiones), due to a debenzylation reaction.On the other hand, the yields in thiones starting from aliphaticdications are higher than the corresponding monocations,suggesting a cooperative reduction at the electrode of the twoimidazolium moieties. The cathodic process was confirmedusing the co-electrogenerated hydrogen to reduce 2,2,2-trifluoroacetophenone to the corresponding alcohol.

AB - The cathodic reduction of dicationic imidazolium bromides,whose spacer is either an aliphatic chain or a xylyl group, leadsto the formation of the corresponding N-heterocyclic carbenes(NHCs), which were isolated as the corresponding thiones, afterreaction with elemental sulfur. The behaviour of the dicationswas compared with the corresponding monocations. Thebehaviour of dicarbenes depends on the nature of the spacer.This study evidenced that dicarbenes deriving from xylyldications are less stable than the corresponding aliphatic ones(giving lower yields in thiones), due to a debenzylation reaction.On the other hand, the yields in thiones starting from aliphaticdications are higher than the corresponding monocations,suggesting a cooperative reduction at the electrode of the twoimidazolium moieties. The cathodic process was confirmedusing the co-electrogenerated hydrogen to reduce 2,2,2-trifluoroacetophenone to the corresponding alcohol.

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